3-Methyl-1-penten-4-yn-3-ol → HCID 19830652, compound

HRID 1493128Notes

Reaction equation

HRID 1493128 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:18])[N:9]([CH3:17])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3I)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]([OH:25])([C:23]#[CH:24])[CH:21]=[CH2:22]>C(N(CC)CC)C.CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[C:7]2[C:8](=[O:18])[N:9]([CH3:17])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:22]#[C:21][C:20]([OH:25])([CH3:19])[CH:23]=[CH2:24])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 978153-Methyl-1-penten-4-yn-3-olHCID 198306597-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 19830652HCID 19830652, compoundYield 63.5%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

7.47 g (20 mmol) of 7-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one, 2.88 g (30 mmol) of 3-methyl-1-penten-4-yn-3-ol, 110 mg of bis(triphenylphosphine)-palladium(II) dichloride and 35 mg of copper(I) iodide were heated to boiling under reflux for 12 hours in 60 ml of triethylamine and 30 ml of dimethyl-formamide. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate. By recrystallization of the residue from acetonitrile there was obtained 4.34 g (63%) of 7-chloro-4,5-dihydro-3-(3-hydroxy-3-methyl-4-penten-1-ynyl)-5-methyl-6H-imidazo[1,5-a][1,4-]benzodiazepin-6-one of melting point 185-187°.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was chromatographed on silica gel
  3. washwhile eluting with ethyl acetate
  4. customBy recrystallization of the residue from acetonitrile

Sources & evidence

ORD record
ord-98f21a798e3c4ee890040954f3efd4f5
Source dataset
uspto-grants-1991_06
Patent number
US05021411

Reaction notes

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